Potassium Carbonate → 2-(4-Aminophenylthio)benzoxazole

HRID 2395338Notes

Reaction equation

HRID 2395338 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[O:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119862-ChlorobenzoxazoleHCID 145104-Aminothiophenol

Product 1

HCID 137183792-(4-Aminophenylthio)benzoxazoleYield 79.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chlorobenzoxazole (0.065 moles, 10.0 g), 4-aminothiophenol (0.065 moles, 8.1 g) and potassium carbonate (0.065 moles, 9.0 g) were stirred for 3 days at room temperature in 250 ml ethanol, filtered, and concentrated. Ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 50% ethyl acetate in hexane to yield 2-(4-aminophenylthio)benzoxazole 12.5 g, 79%. Mass spec (FD) 243. Calculated for C11H10N2OS: C, 64.44; H, 4.16; N, 11.56. Found: C, 64.53; H, 4.22; N, 11.58.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionEthyl acetate was added
  4. washthe solution washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by HPLC over silica gel
  8. washeluted with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1008395171884d5fb0d314a22cee0c1a
Source dataset
uspto-grants-1998_09
Patent number
US05814646

Reaction notes

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